Search for vacation rental homes in Healdsburg

The Two of You in Healdsburg

If you’re looking for a pretty good bottle of wine, it’s no secret that Sonoma County is a smart place to start. In addition to finding a fine pour you’ll find a few other things, too, including a fabulous all-around vacation spot.


Wine sets the tone for an experience in Healdsburg but by no means does it dominate. In addition to strolling through the orchards, farms and vineyards, you’ll also find a lively downtown scene ready to sate all cultural, culinary and creative urges. Along the Russian River is a romantic vacation waiting to happen, so clear a few days from your schedule, grab your favorite person, and see what develops.


Form a solid foundation for your trip by reserving a Vacation Rental in Healdsburg. These properties are everything they should be: elegant, cozy, budget-friendly and warm. Depending on your taste and expectations you’re sure to find just what you’re looking for – most notably, plenty of privacy and a little peace and quiet.


Downtown Healdsburg has an artsy side you’ll quickly grow fond of. A Jazz Festival each June, a healthy scene of local painters, sculptors and jewelry designers, farmers markets, fine restaurants and a few surprises in between will make each journey to the city center a treat. Go back and forth between the peaceful countryside and the heart of Healdsburg in order to ensure that you don’t miss a thing.


California Wine Country could change your definition of a vacation forever. Scout out your favorite spots because a return visit is most definitely in the cards…maybe next time you’ll even bring the kids. Or not.

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  1. Healdsburg Getaway - Wine Country Escape on Russian River — Property 186836

    Vacation House rental in Healdsburg area
    • House
    • 4 bedrooms , sleeps 12
    • 3 bathrooms
    • beach, river
    • accept credit card
    Rates (shown in USD)
    $3200 - $3500 per property per week

  2. Our House Healdsburg Elegance in the Vineyards — Property 215582

    Vacation Estate rental in Healdsburg area
    • Estate
    • 6 bedrooms , sleeps 12
    • 4 bathrooms
    • downtown, rural
    • swimming pool
    Rates (shown in USD)
    $5500 - $5700 per property per week

  3. Beach front with rustic elegance - Premier wine country hideaway - Firefly Lodge — Property 111118

    Vacation House rental in Healdsburg area
    • House
    • 4 bedrooms , sleeps 10
    • 2 bathrooms
    • beach, river
    • accept credit card
    Rates (shown in USD)

  4. Healdsburg 3-4 bedroom Vacation Home with Pool and Spa — Property 191424

    Vacation House rental in Healdsburg area
    • House
    • 4 bedrooms , sleeps 10
    • 3 bathrooms
    • 1 half bathroom
    • rural
    • accept credit card
    Rates (shown in USD)
    $3225 - $3975 per property per week

  5. Kokopelli Country Retreat on 10 acres in the Alexander Valley — Property 187029

    Vacation House rental in Healdsburg area
    • House
    • 3 bedrooms , sleeps 10
    • 2 bathrooms
    • 1 half bathroom
    • swimming pool
    • air-conditioning
    Rates (shown in USD)
    $2500 per property per week

  6. Elegant Palladian Villa in the hills above Geyserville — Property 200479

    Vacation Villa rental in Healdsburg area
    • Villa
    • 6 bedrooms , sleeps 12
    • 6 bathrooms
    • rural
    • swimming pool
    Rates (shown in USD)
    $6650 - $8400 per property per week

  7. Four Sisters Farmhouse — Property 143371

    Vacation House rental in Healdsburg area
    • House
    • 4 bedrooms , sleeps 12
    • 3 bathrooms
    • rural
    • swimming pool
    Rates (shown in USD)
    $4100 per property per week

  8. Dry Creek Valley Home and Vineyard — Property 202349

    Vacation House rental in Healdsburg area
    • House
    • 3 bedrooms , sleeps 10
    • 3 bathrooms
    • 1 half bathroom
    • air-conditioning
    • washing machine
    Rates (shown in USD)

  9. Wine Country Home and Cottages with Beautiful Pool and Hot Tub — Property 173301

    Vacation House rental in Healdsburg area
    • House
    • 2 bedrooms , sleeps 12
    • 1 bathroom
    • river, village
    • accept credit card
    Rates (shown in USD)

  10. Gorgeous Wine Country Home with pool and spa, Central Location, Dreamy & Elegant — Property 163163

    Vacation House rental in Healdsburg area
    • House
    • 5 bedrooms , sleeps 12
    • 2 bathrooms
    • 1 half bathroom
    • mountain, town
    • swimming pool
    Rates (shown in USD)
    $4100 per property per week

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